Reaktion #1528139

ord-680e10130a674bda9d787e67e62d5f31

Reaktionsgleichung

CC(=O)N[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H](CO)O[C@@H]1O
Galβ1-3GalNAcα
CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
UDP-GlcNAc
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-Gal
Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O
8-bromo-cAMP
CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@]3(O)C(=O)C(C)=C[C@@H]23)[C@@H]2C(C)(C)[C@]12OC(C)=O
phorbol 12-myristate 13-acetate
CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O
GalNAcα
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-6
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-6
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
O=P([O-])(O)O.[K+]
KH2PO4
O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
galactose
N=C(N)NCCNS(=O)(=O)c1cccc2cnccc12
H-1004
CCC(CC)COC(C(=O)N(C)CC[NH+](C)C)(c1ccccc1)c1ccccc1.[Cl-]
X-100
CCCC(=O)Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1OC(=O)CCC
dibutyryl cAMP
→
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
N-acetylglucosamine

Edukte

CC(=O)N[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H](CO)O[C@@H]1O
Galβ1-3GalNAcα
CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
UDP-GlcNAc
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-Gal
Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O
8-bromo-cAMP
CCCCCCCCCCCCCC(=O)O[C@@H]1[C@@H](C)[C@@]2(O)[C@@H](C=C(CO)C[C@]3(O)C(=O)C(C)=C[C@@H]23)[C@@H]2C(C)(C)[C@]12OC(C)=O
phorbol 12-myristate 13-acetate
CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O
GalNAcα
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-6
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-6
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP
O=P([O-])(O)O.[K+]
KH2PO4
O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
galactose
N=C(N)NCCNS(=O)(=O)c1cccc2cnccc12
H-1004
CCC(CC)COC(C(=O)N(C)CC[NH+](C)C)(c1ccccc1)c1ccccc1.[Cl-]
X-100
CCCC(=O)Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1OC(=O)CCC
dibutyryl cAMP

Reagenzien

Keine

Lösungsmittel

CC#N
acetonitrile

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Galβ1-3GalNAcα-pNp and GalNAcα-pNp, H-7, H-8 and H-1004 were purchased from Toronto Research Chemicals, Toronto, Canada, UDP-Gal, UDP-GlcNAc, bovine milk β1-4Gal-T (defined as 5-15 units/mg in the presence of lactalbumin), buffer salts and Triton X-100, cholera toxin, dibutyryl cAMP, 8-bromo-cAMP and phorbol 12-myristate 13-acetate (PMA) and TDA were obtained from Sigma. HPLC grade KH2PO4 and acetonitrile were obtained from Fisher Scientific. UDP-6- 3H!-galactose (18.9 Ci/mmol) and UDP-6- 3H!-N-acetylglucosamine (26.8 Ci/mmol) were provided by Amersham and NEN, respectively. C18 Sep-Pak were from Millipore-Waters. Actinomycin D and cycloheximide were purchased from Calbiochem. UDP-6- 3H!-galactose (18.9 Ci/mmole) was purchased from Amersham; dimethysulfoxide (DMSO) from BDH; all-trans-retinoic acid and sodium butyrate from Aldrich; α-modified Eagle's minimum essential medium (α-MEM) and fetal calf serum from Gibco.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05501957uspto-grants-1996_03